Summary
Connect the signed-in iCloud calendar in Keeper.sh and send busy-block copies onto the Google or Outlook calendar that stays empty — or the reverse, sending work hours onto the iPhone they actually check. If the event is missing at icloud.com/calendar, that is Settings, not Keeper.sh.
This page is for anyone whose week lives on iPhone or Mac Calendar and the same hours are missing on another Apple device — an iPhone calendar not syncing to the Mac — or whose Apple Calendar looks correct while work Google or Outlook shows the slot free. Same Apple Account, event missing on one device but present at icloud.com/calendar? Turn iCloud Calendar on, tick the calendar, and stop. Event saved to On My iPhone or On My Mac? Move it to an iCloud calendar and stop. If the leftover job is a Google account on the phone, see /blog/google-calendar-not-syncing-with-iphone. Sharing with a colleague off iCloud? See /blog/how-to-share-iphone-calendar.
The weakest link is that swiping Calendars to refresh, the iCloud Calendar Settings toggle, and icloud.com/calendar only update this Apple Account. A subscription overlay is read-only and refreshes on its own schedule. None of them write a busy block onto Google or Outlook, so iCloud calendars not syncing with work is still an empty calendar on the other side.
Keeper.sh exists to close that gap: it writes private copies, using a placeholder title from the source calendar, onto the calendar that is actually empty. Signed-in iCloud is a valid destination, same as Google and Outlook.
iPhone Calendar refresh, iCloud.com, the Settings toggle, and subscribe / overlay fail that leftover job; the numbered Keeper.sh setup does not.
Swiping Calendars to refresh only updates this iPhone
A meeting typed on the iPhone — clinic, 1:1, standup — sits on Apple Calendar. The same slot is empty on the Mac, or empty at icloud.com/calendar, or Apple Calendar looks correct and work Google Calendar / Outlook shows the hour free. Swiping Calendars to refresh does not fill the other account. Ticking both calendars on the phone only overlays them on this phone.
Apple Community threads show this shape: iCloud Calendar events not syncing from iPhone to MacBook.
Apple's If your iCloud Contacts, Calendars, or Reminders won't sync (Published Date April 04, 2026; fetched 29 Aug 2026) says:
“Open the Calendar app.”
“Tap the Calendars tab.”
“Swipe down on the list to refresh your events.”
“Return to your Home Screen. Wait a few minutes, then open the Calendar app. Tap the Calendars tab, and swipe down to refresh.”
On Mac, the same page says:
“From the View menu, choose Refresh Calendars.”
Apple publishes no general iCloud Calendar sync interval. The only intervals on that page are Birthdays: daily on iOS, hourly on Mac.
“Since the iCloud Birthdays calendar updates daily, changes to birthdays might not appear in the Calendars app until the next day.”
Mac, same page:
“Since the iCloud Birthdays calendar updates hourly, you might not see changes to birthdays in the Contacts or Calendars app for an hour.”
Verdict: Swiping Calendars (or View → Refresh Calendars on Mac) only refreshes this Apple Account on this device. It does not copy events onto Google or Outlook.
iCloud.com does not write events onto Google or Outlook
Apple's Set up iCloud for Calendar on all your devices (fetched 29 Aug 2026) says:
“Go to icloud.com/calendar and sign in to your Apple Account.”
“You can access your iCloud calendars in a web browser on a tablet or computer.”
Treat icloud.com/calendar as the source of truth for this Apple Account. Present on the web, missing on a device → device. Missing on the web too → never saved to iCloud, often because it was saved to On My iPhone or On My Mac. That diagnosis does not put the event on Google.
Apple's Share a calendar on iCloud.com (fetched 29 Aug 2026) says: "You need to be on a tablet or computer to use Calendar on iCloud.com." From there, calendar info in the sidebar offers Sharing With (private) or Public Calendar.
“When you share a calendar privately, your invitees must have an Apple Account and use iCloud in order to use the calendar.”
“Only the calendar’s owner can share a private calendar.”
“Allow editing: Allows the invitee to create, edit, and delete events, and track invitation responses.”
“Read-Only: Allows the invitee to view, but not edit, the calendar.”
“When you share a calendar publicly, your invitees automatically receive an email that includes the calendar URL. An invitee doesn’t need to be an iCloud user to accept an invitation to view a shared public calendar.”
“Only the calendar’s owner can share and make changes to a public calendar.”
“Share the calendar with a link: Select Copy, then paste the link where you want to share it”
Verdict: icloud.com/calendar tells you whether iCloud has the event. Sharing from it does not put a busy block on Google or Outlook.
The iCloud Calendar Settings toggle only turns iCloud on for this Apple Account
Apple's Set up iCloud for Calendar on all your devices (fetched 29 Aug 2026) says:
“Make sure you're signed in to the same Apple Account on each device. If you're not signed in to your Apple Account on a device, or the device has the Calendars feature turned off, you won't be able to access your iCloud calendars on the device.”
For iOS 17, iPadOS 17, or later:
“Tap See All (or Show All), tap iCloud Calendar, then turn on “Use on this [device].””
And for the iPhone Calendar list, same page:
“Tap Calendars at the bottom of the screen, then select the calendars you want to view in the iCloud section.”
Apple's If your iCloud Contacts, Calendars, or Reminders won't sync (Published Date April 04, 2026; fetched 29 Aug 2026) says:
“Make sure you signed in to iCloud with the same Apple Account on all of your devices. Then check that you turned on Contacts, Calendars and Reminders in your iCloud settings.”
“Open the Calendar app and tap the Calendars button. Make sure that all iCloud calendars are selected.”
“If you store and edit your events in iCloud instead of another place, like On My Mac, Exchange, or Google, then iCloud automatically updates your calendars.”
That last sentence is iCloud updating iCloud. Exchange and Google are named as other places, not as destinations iCloud writes into.
Default Calendar, same page:
“Set an iCloud calendar as the default calendar: Tap Settings, tap Apps, then tap Calendar. … Tap Default Calendar. Tap a calendar under iCloud to make it your default.”
Sync lookback, same page:
“Tap Settings, tap Apps, then tap Calendar. In iOS 17 or earlier, tap Settings, then tap Calendar. Tap Sync. If All Events is selected, choose a specific timeframe instead, like Events 1 Month Back. If a specific timeframe is selected, choose All Events instead.”
That is the control in iPhone calendar missing my appointments before May.
iCloud storage can also matter. Apple's Manage your iCloud storage (Published Date January 14, 2026; fetched 29 Aug 2026) says:
“If you run out of iCloud storage, your device won’t back up to iCloud, new photos and videos won't upload to iCloud Photos, and iCloud Drive and other iCloud apps won't stay up to date across your devices.”
Calendar is an iCloud app; "other iCloud apps" is what Apple printed.
Verdict: The iCloud Calendar Settings toggle, Default Calendar, and Sync lookback fix same-account iCloud being off or hidden. If that was the whole job, stop. They will not write the event onto Google or Outlook. Keeper.sh does not belong on a toggle that was off.
Subscribe and overlay are not a copy onto another account
Two leftover jobs live here: a calendar that came from a link will not update, and ticking calendars on the phone is not a copy onto another account.
On Mac, subscription controls sit under Auto-refresh. Apple's Subscribe to calendars on Mac (fetched 29 Aug 2026) says:
“The events shown in a subscription calendar are controlled by the provider. You can’t edit calendars you are subscribed to (for example, the Holidays calendar).”
“Click the Auto-refresh pop-up menu, then choose how often to update the calendar.”
Apple's Refresh calendars on Mac says:
“A calendar you subscribe to has a Subscription button next to its name.”
“Subscribed calendars can be refreshed automatically.”
“Control-click the calendar’s name, then choose Get Info.”
“Click the Auto-refresh pop-up menu, then choose an option.”
Do not mix Auto-refresh with account-level Refresh Calendars. The Push sentence on that page is for shared calendars in an account:
“If you choose Push, the account is updated automatically when you make a change on any of your devices that use the same account, or when someone makes a change to a shared calendar in that account.”
Apple publishes no Auto-refresh interval values.
On iPhone, the path is Add Subscription Calendar. Apple's Add calendar subscriptions in iCloud (Published Date May 22, 2026; fetched 29 Aug 2026) says:
“Subscribe to an external, read-only calendar: Tap Add Subscription Calendar, enter the URL of the .ics file you want to subscribe to (and any other required server information), then tap Find.”
For iOS 26 or later:
“Tap Add Calendar, then tap Add Subscription Calendar.”
“Enter the calendar's web address, then tap Find.”
On iOS 18 or earlier, the same path ends with Subscribe instead of Find.
Apple publishes no refresh interval for iPhone subscriptions either. If a subscribed calendar looks stale, see /guides/subscribed-calendar-out-of-date. Keeper.sh cannot make Calendar ask sooner. A pasted share / ICS / subscribe link is pull-only in Keeper.sh — never a destination.
For overlay, Apple's Set up multiple calendars on iPhone says:
“Select the calendars you want to view.”
Apple's If you have duplicate events on your iCloud Calendar (Published Date May 15, 2025) says:
“Select or deselect the calendar’s checkbox in the Calendar list to show or hide a calendar’s events.”
Verdict: Subscribe / Auto-refresh / ticking Calendars overlays a read-only feed or this device's view. It does not put a private busy copy on Google or Outlook.
Put Apple Calendar busy blocks on the other calendar with Keeper.sh
Connection is the leftover job on this page: events are correct in Apple Calendar / iCloud and need to exist as busy blocks on Google, Outlook, or another signed-in iCloud calendar. A times-only feed is for sharing with colleagues off iCloud; see /blog/how-to-share-iphone-calendar and /recipes/share-when-you-are-busy. Keeper.sh belongs here when the leftover job is a write copy. Native iCloud share / ICS / subscribe links stay read-only.
You need a Keeper.sh account. Connecting copies nothing by itself. /docs/accounts-and-calendars: "Connecting copies nothing by itself. Events only move once you send them to another calendar."
-
Connect the iCloud account that holds the calendar. iCloud needs an app-specific password, never the Apple Account password. Click-by-click details are in /docs/accounts-and-calendars. Keeper.sh: "iCloud and Fastmail — an app-specific password, made in their settings."
-
Connect the destination account — the Google or Outlook calendar that stays empty, or another signed-in iCloud account if that is the leftover job. Signed-in iCloud (Apple ID + app-specific password) is a valid destination: one sign-in, pull and push. A pasted share / ICS / subscribe link is not.
-
Open the source calendar. Under Send Events to Calendars, tick the destination. One tick is one mapping. /docs/sending-events-to-another-calendar: "Each calendar you tick becomes one connection. Events are copied into it, one way, and the copies are kept corrected as the originals change."
-
Leave the privacy defaults. Copies use a placeholder title from the source calendar; description and location stay hidden. Those toggles are Pro. /docs/what-a-copied-event-shows.
-
Confirm on the destination: a real event, named after the source calendar, no notes, no location, no guest list.
Busy-block both ways is two mappings (A→B and B→A), same as Google and Outlook. One signed-in iCloud account is enough — not two Apple IDs. A create still lands on the calendar that owns the event. Guest lists stay off; title and description stay private unless opted in.
App-specific password (required for iCloud). Apple's Sign in to apps with your Apple Account using app-specific passwords (Published Date October 08, 2025; fetched 29 Aug 2026) says:
“App-specific passwords allow you to sign in to your Apple Account in apps made by developers other than Apple.”
“To generate and use app-specific passwords, your Apple Account must be protected with two-factor authentication.”
“You can have up to 25 active app-specific passwords. If you need to, you can revoke passwords individually or all at once.”
“After you revoke a password, the app using that password will be signed out of your account until you generate a new password and sign in again.”
“Any time you change or reset your primary Apple Account password, all of your app-specific passwords are revoked automatically to protect the security of your account. You need to generate new app-specific passwords for any apps that you want to continue using.”
Apple documents the path as account.apple.com → Sign-In and Security → App-Specific Passwords → Generate an app-specific password. If a working Keeper.sh iCloud connection later goes quiet after an Apple password change, this is why — generate a new app-specific password and paste it into Connect Apple Calendar. This is Apple's behaviour, not a Keeper.sh defect.
If nothing arrives, see /guides/event-has-not-arrived. Removing a connection stops new copies; copies already written stay (/docs/sending-events-to-another-calendar: "Untick the calendar in Send Events to Calendars and new events stop being copied. Events already copied stay where they are.").
Cadence and price. From /docs/plans-and-limits (Updated August 14, 2026; fetched 29 Aug 2026) and /docs/sending-events-to-another-calendar:
- Sources are read every minute on every plan.
- Free destinations write every 30 minutes.
- Pro writes every minute. On Pro, a change you make in Google or Outlook shows up on the other calendar the moment you make it. iCloud stays on the timer. "iCloud, Fastmail and other CalDAV calendars are checked on a timer on either plan, because Apple publishes no way for a calendar tool to be told an event changed."
- Free: 2 accounts, 3 connections, 1 shareable link, 25 MCP/API calls a day.
- Pro: $5/month or $45/year. "Pro is $5 a month, or $45 a year paid annually."
- Guest lists are never copied, on any plan.
Why a Keeper.sh copy instead of refresh or a subscription
- Swipe-to-refresh and the iCloud Calendar toggle only update this Apple Account. A Keeper.sh connection writes a private copy onto the calendar that stayed empty.
- icloud.com share required an Apple Account or handed a full-details public URL. Keeper.sh copies use a placeholder title; description and location stay hidden.
- Subscribe / overlay stacked a read-only feed or a view on this phone. Keeper.sh copies exist as real events on the destination.